WO2011007102A1 - Use of at least one omega-3 fatty acid and of at least one polyphenol for the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid - Google Patents
Use of at least one omega-3 fatty acid and of at least one polyphenol for the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid Download PDFInfo
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- WO2011007102A1 WO2011007102A1 PCT/FR2010/051486 FR2010051486W WO2011007102A1 WO 2011007102 A1 WO2011007102 A1 WO 2011007102A1 FR 2010051486 W FR2010051486 W FR 2010051486W WO 2011007102 A1 WO2011007102 A1 WO 2011007102A1
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- WIPO (PCT)
- Prior art keywords
- acid
- polyphenol
- use according
- omega
- composition
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- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 24
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 24
- 235000020660 omega-3 fatty acid Nutrition 0.000 title claims abstract description 20
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 title claims abstract description 8
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 title claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 7
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 7
- 229940012843 omega-3 fatty acid Drugs 0.000 title claims description 12
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 title claims description 9
- 241001465754 Metazoa Species 0.000 claims abstract description 28
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims abstract description 14
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- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 claims abstract description 10
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Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates, in general, to the use of at least one omega-3 fatty acid and at least one polyphenol for the endogenous synthesis of eicosapentaenoic acid and docosahexaenoic acid.
- human body and in particular supplementing this diet with a composition containing a mixture of at least one omega-3 fatty acid with a polyphenol for increasing the endogenous synthesis of omega-3 fatty acids at 20 or 22 carbon atoms (termed very long chain omega-3 fatty acids or TLC).
- the main omega-3 fatty acids are ⁇ -linolenic acid or ⁇ 3 ⁇ (18: 3, ALA), eicosapentaenoic acid (20: 5, EPA) and docosahexaenoic acid (22: 6, DHA). They are called essential fatty acids because the animal body, especially human, does not know how to synthesize them or knows how to synthesize them in insufficient quantity. A minimal and regular intake of food is considered necessary by the experts.
- TLC fatty acids including EPA and DHA
- Nutritionists therefore recommend regular fish consumption. Nevertheless, the increase in fish consumption around the world is leading to overfishing and the desertification of the seas.
- An alternative to overfishing is the existence of farmed fish on marine farms. Plankton containing significant amounts of DHA and EPA is essential for feeding farmed fish. The plankton is collected by the harvesters, which leads to the impoverishment of the seas. This chain of events is leading to ecological upheaval and violent conflict with the fish industry.
- ALA is found in plants, but ALA is not efficiently transformed into TLC by animals, especially humans.
- the use of ALA can not therefore, according to experts provide a lack of intake of omega-3 TLC of marine origin.
- the present invention provides an alternative to the dietary consumption of TLC fatty acids of essentially marine origin.
- the present invention relates to the use of at least one omega-3 fatty acid selected from ⁇ -linolenic acid (ALA) and stearidonic acid (SA) and from at least one polyphenol, as agent enhancing the endogenous synthesis of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), for the preparation of a dietary, dietetic or pharmaceutical composition for administration to a human or an animal.
- omega-3 fatty acid selected from ⁇ -linolenic acid (ALA) and stearidonic acid (SA) and from at least one polyphenol, as agent enhancing the endogenous synthesis of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)
- EPA eicosapentaenoic acid
- DHA docosahexaenoic acid
- the polyphenol may be chosen from apigenin, luteolin, chlorogenic acid, caffeic acid, ferulic acid, coumaric acids, hydroxycinnamic acid, acid salicylic acid, gallic acid, quercetin, eriodyctiol, catechin, epicatechin, epigallocatechin gallate, isorhamnetin, kaempherol, hesperetin, naringenin, phloretin, enterolactone, enterodiol , oleuropein, hydroxytyrosol, resveratrol, myricetin, rutin, phenolic acids, stilbenes, flavonoids and lignans.
- the polyphenol is an anthocyanin.
- the anthocyanin is chosen from cyanidine, delphidine, malvidine, peonidine, pelargonidine and petunidine.
- the composition further comprises a compound selected from vitamins, mineral salts and trace elements.
- the composition is in the form of granules, powder, liquid, semi-liquid.
- the composition when it is a food or dietetic composition, it may be an oil, a margarine, a yogurt, a cheese, a bread, a rusk, a cake, a biscuit, a meal replacement, a cream, a chocolate bar, a cereal bar, or a compote made from fruit.
- dietary or dietetic composition means any type of product intended to be ingested by the animal organism, in particular human.
- dietary supplements are products intended to be ingested, in addition to the current diet, in order to compensate for the insufficiency of daily intake of certain compounds.
- the food or dietetic composition of the invention can be in the form of granules, of powder, in liquid form in a natural way or be suspended or dissolved. It can be in a form adapted to the addition to the diet of an animal, or any other product constituting a food intake.
- the composition according to the invention can be in dry, pasty, semi-pasty, liquid or semi-liquid form. These include, for example, food products, beverages, dietary supplements and nutraceuticals.
- oils margarines and other fats, yoghurts, cheeses, including especially fresh cheeses and derived products, fermented products, products of the present invention.
- dairy products, bread, rusks, and other cereal or derived products (pasta for example), cakes and cookies, meal replacements, snack foods in general, foods for children, babies and infants, creams, desserts, ice creams, chocolate bars, cereal bars, fruit compotes.
- the composition is in a form suitable for adding an animal to the feed ration.
- animal is meant more particularly, in addition to humans, livestock and especially grazing animals (including cattle raised for meat, milk and other dairy products, cheese and leather, sheep raised for meat, wool and cheese; goats; pigs), rabbits, poultry (chickens, chickens, turkeys, ducks, geese and others) reared for meat and meat products including eggs, aquatic animals (eg farm animals, fish, shrimps, oysters and mussels), recreational and companion animals (including horses, dogs, cats, pet birds, aquarium fish), laboratory animals (especially rats and mouse).
- livestock and especially grazing animals including cattle raised for meat, milk and other dairy products, cheese and leather, sheep raised for meat, wool and cheese; goats; pigs
- poultry chickens, chickens, turkeys, ducks, geese and others
- recreational and companion animals including horses, dogs, cats, pet birds, aquarium fish
- laboratory animals especially rats and mouse
- compositions in particular but not exclusively, the compositions in solid, liquid, pasty semi-pasty, semi-liquid form.
- a pharmaceutically acceptable excipient This is chosen so as to be suitable for the formulation of the two compounds of the composition (fatty acid and polyphenol).
- the excipient is adapted to the desired route of administration and the nature of the desired dosage form.
- the pharmaceutical compositions of the invention are available in all galenic forms suitable for administration. Said galenic forms may especially consist of: tablets, capsules, powders, granules, lyophilisates, drinkable solutions, syrups, suspensions and suppositories. This list is not exhaustive.
- tablette refers to all kinds of tablets including effervescent tablets, dispersible tablets and orodispersible tablets.
- composition of the invention when in the form of a granule or tablet, it may be in the form of a coating, so as to avoid the enzymatic destruction which takes place at a certain pH, and at the same time so as to allow the release controlled the active compound in another part of the digestive tract.
- the composition according to the invention may also be in the form of sustained release or controlled release tablets.
- omega-3 fatty acid polyunsaturated fatty acid, that is to say having at least one double bond, and whose first double bond connects the carbon atoms 3 and 4.
- the fatty acid may have 3, 4 or 5 double bonds.
- the fatty acid of the omega-3 group can have 18, 20, 22 or 24 carbon atoms.
- the fatty acid of the omega-3 group may be an ⁇ -linolenic acid (ALA; C18: 3), a stearidonic acid (SA; C 1 8: 4), an eicosatetraenoic acid (ETA; C20: 4) , an eicosapentaenoic acid (EPA; C20: 5), an acid docosapentaenoic acid (DPA; C22: 5) or a mixture of at least two of these compounds.
- ALA ⁇ -linolenic acid
- SA stearidonic acid
- ETA eicosatetraenoic acid
- EPA eicosapentaenoic acid
- DPA acid docosapentaenoic acid
- the fatty acid of the omega-3 group is ⁇ -linolenic acid (ALA; C 1 8: 3) or stearidonic acid (SA; C18: 4).
- Polyphenols are a family of organic molecules characterized by the presence of several phenolic groups. Their structure is more or less complex.
- the polyphenols are chosen from those generally present in so-called Mediterranean foods, for example grapes, wine, citrus fruits, whole grains, legumes (in particular lentils, peas, beans), teas, coffee , olive oil, olives, linseed, linseed oil, walnuts, walnut oil, fruits (including cherry, plum, raspberry, blueberries, strawberries, currants, blackberries, cranberries ) and vegetables (including cucumbers, celery, zucchini, crucifers, including broccoli, artichoke, garlic, eggplant, tomatoes, red onions, peppers, carrots), and herbs (including thyme, basil, parsley, coriander, oregano, rosemary, chives, sage).
- the polyphenols are also chosen from those generally present in foods containing fats, for example the polyphenols of cocoa, rapeseed, or aztec maize.
- the polyphenols are chosen from apigenin, luteolin, chlorogenic acid, caffeic acid, ferulic acid, coumaric acids, hydroxycinnamic acid, and acid.
- the polyphenols are chosen from phenolic acids, stilbenes, flavonoids and lignans.
- the polyphenols are flavonoids, they are selected from anthocyanins and proanthocyanidins, flavonols, flavones, flavanones, flavanols, isoflavones and chalcones.
- anthocyanins are cyanidin, delphidine, malvidine, peonidine, pelargonidine and petunidine.
- the composition further comprises a compound selected from vitamins, mineral salts and trace elements.
- Vitamins include vitamin C (ascorbic acid), vitamin B3 (nicotinamide), vitamin B5 (pantothenic acid), vitamin B6 (pyridoxine), vitamin B2 (riboflavin), vitamin B1 (thiamine) , vitamin B9 (folic acid), vitamin B8 (biotin), vitamin B12 (cyanocobalamin), vitamin D (calciferol), vitamin E (tocopherol), vitamin A (retinol) and vitamin K.
- mineral salts mention may be made of calcium (Ca), iron (Fe), magnesium (Mg), sodium (Na), phosphorus (P), potassium (K) and sulfur (S).
- trace elements mention may be made of aluminum (Al), arsenic (As), boron (B), chlorine (Cl), chromium (Cr), cobalt (Co), copper ( Cu), fluorine (F), iodine (I), manganese (Mn), molybdenum (Mo), nickel (Ni), lead (Pb), silicon (Si), selenium (Se) ), vanadium (V) and zinc (Zn).
- compositions of the present invention are prepared by mixing said compounds.
- the dietary or pharmaceutical food composition comprises a) from 1 to 99% by weight of at least one omega-3 fatty acid selected from ⁇ -linolenic acid and stearidonic acid; and b) from 99 to 1% by weight of said at least one polyphenol.
- said at least one omega-3 fatty acid selected from ⁇ -linolenic acid and stearidonic acid is present between 10 and 90%, preferably between 20 and 80% and more preferably between 30 and 80%. and 70% by weight of the total weight of the composition.
- said at least one polyphenol is present between 10 and 90%, preferably between 20 and 80% and more preferably between 30 and 70% by weight of the total weight of the composition.
- the foods are prepared according to the protocol described in Tou Stammsian et al. (J Nutr 2008; 38: 747-752). Each diet is equivalent in energy terms with 67% of carbohydrates, 23% of proteins and 10% of lipids.
- the fatty acid composition of each diet is given in Table 1.
- the anthocyanins used in this test are derived from a non-genetically transformed corn so as to render it rich in anthocyanins.
- the feed ration of the rats contains 20% processed corn, this percentage being relative to the total weight of maize present in the feed (in the form of pellets).
- PUFA polyunsaturated fatty acids
- triglyceride and cholesterol levels are not significantly affected by anthocyanin consumption.
- the plasma levels of oleic, myristic and palmitic fatty acids are similar to those of rats not supplemented with polyphenol (ACN-free).
- SFA, MUFA, PUFA and n-6 (or omega-6) levels are similar in both groups.
- the levels in n-3 (or omega-3) and the ratio n-3: n-6 are nevertheless significantly increased after consumption of polyphenol (ACN-rich). In this respect, EPA and DHA levels are increased by 41% and 16% respectively.
- n-3 and n-6 levels are not significantly different.
- n-3: n-6 ratio increases significantly in animals receiving the combination of Palm Oil + anthocyanin.
- EPA and DHA levels are increased by 25% and 10% respectively.
- n-6 ratios were increased in animals receiving the EPA + DHA + anthocyanin combination.
- EPA on the one hand
- DHA on the other, are increased by 24% and 16%, respectively.
- Palmitic 16 0 21.94 ⁇ 0.65 20.57 ⁇ 0.68
- LA Linoleic
- ALA ⁇ -linolenic
- PUFA polyunsaturated fatty acids
- Palmitic 16 0 22.65 ⁇ 0.27 22.96 ⁇ 0.56
- PUFA polyunsaturated fatty acids
- Palmitic 16 0 22.39 ' ⁇ 0.26 21.91 ⁇ 0.73
- Olieic 18 ln-9 9.35 ⁇ 0.34 10.07 ⁇ 0.44
- LA Linoleic
- ALA ⁇ -linolenic
- PUFA polyunsaturated fatty acids
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2768050A CA2768050A1 (en) | 2009-07-15 | 2010-07-15 | Use of at least one omega-3 fatty acid and of at least one polyphenol for the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid |
US13/383,290 US20120202778A1 (en) | 2009-07-15 | 2010-07-15 | Use of at least one omega-3 fatty acid and of at least one polyphenol for the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid |
EP10752018A EP2453888A1 (en) | 2009-07-15 | 2010-07-15 | Use of at least one omega-3 fatty acid and of at least one polyphenol for the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid |
AU2010272346A AU2010272346A1 (en) | 2009-07-15 | 2010-07-15 | Use of at least one omega-3 fatty acid and of at least one polyphenol for the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0954900A FR2948025B1 (en) | 2009-07-15 | 2009-07-15 | COMPOSITION COMPRISING POLYPHENOL AND OMEGA-3 FATTY ACID |
FR0954900 | 2009-07-15 |
Publications (1)
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WO2011007102A1 true WO2011007102A1 (en) | 2011-01-20 |
Family
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PCT/FR2010/051486 WO2011007102A1 (en) | 2009-07-15 | 2010-07-15 | Use of at least one omega-3 fatty acid and of at least one polyphenol for the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid |
Country Status (6)
Country | Link |
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US (1) | US20120202778A1 (en) |
EP (1) | EP2453888A1 (en) |
AU (1) | AU2010272346A1 (en) |
CA (1) | CA2768050A1 (en) |
FR (1) | FR2948025B1 (en) |
WO (1) | WO2011007102A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8168611B1 (en) | 2011-09-29 | 2012-05-01 | Chemo S.A. France | Compositions, kits and methods for nutrition supplementation |
US8183227B1 (en) | 2011-07-07 | 2012-05-22 | Chemo S. A. France | Compositions, kits and methods for nutrition supplementation |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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MX370090B (en) | 2013-02-01 | 2019-10-25 | Centro De Investig En Alimentacion Y Desarrollo A C | Method and system for the integral treatment of wastewater from the maize industry. |
PL3054777T3 (en) * | 2013-10-07 | 2018-10-31 | Zinzino Ab | Edible lipid composition comprising stearidonic acid and olive oil |
EP4312576A1 (en) * | 2022-05-12 | 2024-02-07 | Industrial Técnica Pecuaria S.A. | Hydroxytyrosol for processing animal by-products |
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US8183227B1 (en) | 2011-07-07 | 2012-05-22 | Chemo S. A. France | Compositions, kits and methods for nutrition supplementation |
US8168611B1 (en) | 2011-09-29 | 2012-05-01 | Chemo S.A. France | Compositions, kits and methods for nutrition supplementation |
US8545896B2 (en) | 2011-09-29 | 2013-10-01 | Chemo S. A. France | Compositions, kits and methods for nutrition supplementation |
Also Published As
Publication number | Publication date |
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US20120202778A1 (en) | 2012-08-09 |
FR2948025B1 (en) | 2013-01-11 |
FR2948025A1 (en) | 2011-01-21 |
CA2768050A1 (en) | 2011-01-20 |
AU2010272346A1 (en) | 2012-02-16 |
EP2453888A1 (en) | 2012-05-23 |
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